Potassium Carbonate → HCID 57586498, compound

HRID 420404Notes

Reaction equation

HRID 420404 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=O)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27]C)=[O:25])C.[C:30](=O)([O-])[O-].[K+].[K+].C/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N>CO>[CH3:1][O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:30])[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57586512HCID 57586512, compoundHCID 178502985HCID 178502985, compound

Product 1

HCID 57586498HCID 57586498, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 0° C. solution of 4-[2-(2-Ethoxycarbonyl-ethyl)-3-(6-oxo-hexyl)-phenoxy]-butyric acid ethyl ester (7.0 g, 17.24 mmol) and potassium carbonate (7.14 g, 51.72 mmol) in MeOH (200 mL), the Ohira's reagent (ref. cited in Synlett, 1996, 521) (6.3 g, 32.8 mmol) in MeOH (50 mL) was added slowly. The cooling bath was removed upon the end of addition and the reaction mixture stirred at room temperature for 5 hr. The reaction was then extracted with EtOAc and brine. The combined organic layers were dried over sodium sulfate then evaporated under vacuo. The crude material was purified by column chromatography using 50% EtOAc-Hexane as eluant to give the title compound (4.6 g, 71%) as a light yellow oil. HR-ES(+): calculated for C22H30O5 (M+Na)1+ 397.1985, found 397.1985.

Workup

  1. customThe cooling bath was removed upon the end of addition
  2. extractionThe reaction was then extracted with EtOAc and brine
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthen evaporated under vacuo
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-c283fb61c69a4aafb6146e4644833d3c
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

Loading…